The longtime Oakland councilman is giving up sure reelection in order to take on Rebecca Kaplan, the most popular elected official in the city.

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Two years ago, Councilwoman Rebecca Kaplan came close to winning the Oakland mayor's race. Before being eliminated in the next-to-last round of ranked-choice balloting, Kaplan trailed Jean Quan by just 2,314 votes — or 2 percentage points. And if Kaplan had finished…